Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-08-22
2002-06-18
Yamnitzky, Marie (Department: 1774)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C546S153000, C546S155000, C546S159000, C546S160000, C546S171000, C546S173000, C546S176000, C546S178000
Reexamination Certificate
active
06407242
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a quinoline compound suited for use in a luminous layer of an electro-luminescence element, the electro-luminescence element and a fluorescent material by using said compound, and a preparation process of said compound.
The invention also relates to a zinc halogenide complex suited for use in a luminous layer of an electro-luminescence element or an ultraviolet absorption material, the electro-luminescence element and the ultraviolet absorption material by using said complex, and a preparation process of said complex.
The invention further relates to a zinc complex suited for use in a luminous layer of an electro-luminescence element or an ultraviolet absorption material, the electro-luminescence element and the ultraviolet absorption material by using said complex, and a preparation process of said complex.
2. Related Art of the Invention
In recent years, a great deal of research a great deal of research on fluorescent materials and luminescent materials have been carried out in order to use these materials for electro-luminescence (EL) elements.
A quinoline having the formula (7):
has been known to have fluorescent property as described in Liebigs Ann. Chem., vol.315, p.303(1901) and Chem. Ber., vol.100, p. 2261-2273 (1967).
On the other hand, the EL elements have recently attained a great progress. Luminous layers and positive hole transport layers have been investigated and are approaching practical use [Tsutsui, Saito et. al., Japan Journal of Applied Physics, vol.27, No.2, L269 (1988); vol.27, No.4,L713(1988)].
Aromatic compounds which exhibit fluorescence in the ultraviolet to visible region have been known [I. B. Berlman, Handbook of Fluorescence Spectra of Aromatic Molecules, published from Academic Press].
Further, inorganic compounds such as titanium dioxide and zinc oxide, and organic compounds such as benzophenone, benzotriazole and other compounds having a triazine structure have been known as ultraviolet absorption materials as disclosed in Japanese Laid-Open Patent Sho 64-20248.
SUMMARY OF THE INVENTION
The first object of the invention is to provide an excellent material as an EL material and a useful preparation process of the material.
The second object of the invention is to provide an excellent material as a fluorescent material and a useful preparation process of the material.
Further, the third object of the invention is to provide an excellent material as an ultraviolet absorption material and a useful preparation process of the material.
These objects can be achieved by the following aspects of the present invention.
(1) A quinoline compound and a tautomer of the same which are represented by the formula (1):
where each of R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, R
9
and R
10
is individually a hydrogen atom, halogen atom, cyano, amino, substituted or unsubstituted alkyl having two or more carbon atoms substituted or unsubstituted aryl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted N-alkylamino, substituted or unsubstituted N,N-dialkylamino, substituted or unsubstituted N-arylamino, substituted or unsubstituted N,N-diarylamino or substituted or unsubstituted N-alkyl-N-arylamino group, except the case where all of R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, R
9
and R
10
is a hydrogen atom.
(2) A zinc halogenide complex and a tautomer of the same which are represented by the formula (2):
where each of R
11
, R
12
, R
13
, R
14
, R
15
, R
16
, R
17
, R
18
, R
19
, R
20
, R
21
, R
22
, R
23
, R
24
, R
25
, R
26
, R
27
, R
28
, R
29
and R
30
is individually a hydrogen atom, halogen atom, nitro, cyano, hydroxy, amino, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted N-alkylamino , substituted or unsubstituted N,N-dialkylamino, substituted or unsubstituted N-arylamino, substituted or unsubstituted N,N-diarylamino or substituted or unsubstituted N-alkyl-N-arylamino group, and each of X
1
and X
2
is individually a fluorine, chlorine, bromine or iodine atom.
(3) A zinc complex and tautomer of the same which are represented by the formula (3):
where each of R
31
, R
32
, R
33
, R
34
, R
35
, R
36
, R
37
, R
38
, R
39
, R
40
, R
41
, R
42
, R
43
, R
44
, R
45
, R
46
, R
47
, R
48
, R
49
and R
50
is individually hydrogen atom, halogen atom, nitro, cyano, hydroxy, amino, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted N-alkylamino, substituted or unsubstituted N,N-dialkylamino, substituted or unsubstituted N-arylamino, substituted or unsubstituted N,N-diarylamino or substituted or unsubstituted N-alkyl-N-arylamino group.
(4) A quinoline compound which has peak intensity at a Bragg angle (2 &thgr;) of 12.8°, 15.2°, 18.3°, 22.5°, 25° and 28.4° on a X-ray diffraction spectrum and is shown by the formula (7):
(5) A quinoline compound of the formula (7) wherein the peak intensity ratio of the Bragg angle (2&thgr;) of 12.8° to the Bragg angle (2&thgr;) of 15.2° is 0.7 or less.
(6) A preparation process of a quinoline compound and a tautomer of the same which are represented by the formula (4):
where each of R
51
, R
52
, R
53
, R
54
R
55
, R
56
, R
57
, R
58
, R
59
, R
60
, is individually hydrogen atom, halogen atom, nitro, cyano, hydroxy, amino, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted N-alkylamino, substituted or unsubstituted N,N-dialkylamino, substituted or unsubstituted N-arylamino, substituted or unsubstituted N,N-diarylamino or substituted or unsubstituted N-alkyl-N-arylamino group, comprising reacting a quinoline derivative represented by the formula (5)
where each of Y
1
, Y
2
, Y
3
, Y
4
, Y
5
and Y
6
is a hydrogen atom, halogen atom, nitro, cyano, hydroxy, amino, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkoxy substituted or unsubstituted aryloxy, substituted or unsubstituted N-alkylamino, substituted or unsubstituted N,N-dialkylamino, substituted or unsubstituted N-arylamino, substituted or unsubstituted N,N-diarylamino or substituted or unsubstituted N-alkyl-N-arylamino group, and a phthalimide derivative represented by the formula (6):
where each of Y
7
, Y
8
, Y
9
and Y
10
is individually a hydrogen atom, halogen atom, nitro, cyano, hydroxy, amino, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted N-alkylamino, substituted or unsubstituted N,N-dialkylamino, substituted or unsubstituted N-arylamino, substituted or unsubstituted N,N-diarylamino or substituted or unsubstituted N-alkyl-N-arylamino group, with zinc halogenide in an organic basic solvent and successively treating with an inorganic acid.
(7) A preparation process of a quinoline compound and a tautomer which are represented by the formula (4) wherein a phthalimide derivative represented by the formula (6) is in a molar ratio of 0.5 to 2.0 to a quinoline derivative represented by the formula (5).
(8) A preparation process of a quinoline compound and a tautomer which are represented by the formula (4) wherein a phthalimide derivative represented by the formula (6) is in a molar ratio of 1.1 to 2.0 to a quinoline derivative represented by the formula (5),
(9) A preparation process of a quinoline compound represented by the formula (4) and a tautomer of the same comprising treating with an inorganic acid a zinc halogenide complex represented by the formula (2) and a tautomer of the same.
(10) A preparation process of a quinoline compound represented by the formula (4) and a tautomer of the same comprising treating with an inorganic acid a zinc co
Ikuta Hideki
Ito Hisato
Nagayoshi Tatsuya
Ogiso Akira
Okuma Tadashi
Mitsui Chemicals Inc.
Yamnitzky Marie
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